One Bold Cardinals Free Agent Target Who Checks Every Box

The St. Louis Cardinals could use a veteran starting pitcher and an old friend would make a lot of sense in free agency.

Jul 10, 2026; Detroit, Michigan, USA; Detroit Tigers starting pitcher Jack Flaherty (9) throws a pitch in the rain against the Philadelphia Phillies in the fifth inning at Comerica Park. Mandatory Credit: Lon Horwedel-Imagn Images | IMAGN IMAGES via Reuters Connect

When the market opens and free agency kicks off across the league this winter, the St. Louis Cardinals likely aren't going to be a team that goes out and hands someone a massive deal.

It's just not where the Cardinals are in their rebuild. Arguably, the Cardinals aren't very far from making a run at a wild-card spot, but they aren't just one or two pieces away from being legit World Series contenders. For the Cardinals to get to that point, they need to add some pieces and also get big jumps from the young guys already on the roster. Jordan Walker took a leap in 2026. The club will need more of that from other young guys on the roster, like Leo Bernal, Joshua Baez and maybe even Masyn Winn. Winn has been excellent defensively, but his bat needs to take a step forward.

This winter, the Cardinals should be shopping for a veteran starting pitcher to pair with the young rotation the club has, similar to what they did with Dustin May. A guy they should target and would check a lot of boxes is old friend Jack Flaherty.

The Cardinals Should Reunite With Jack Flaherty

Jul 20, 2026; Chicago, Illinois, USA; Detroit Tigers pitcher Jack Flaherty delivers the ball during the first inning against the Chicago Cubs at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images | IMAGN IMAGES via Reuters Connect

Cardinals fans will remember Flaherty well. He was a first-round pick by the organization back in 2014 and made his big league debut in 2017. He spent six-plus seasons with the organization before being traded to the Baltimore Orioles ahead of the 2023 trade deadline. While in St. Louis, he flashed superstar potential. Back in 2019, he had a 2.75 ERA in 33 starts for the Cardinals in his third season in the big leagues. He had a 3.38 ERA in 28 starts the year before. Unfortunately, injuries derailed him afterward.

In 2024, he looked more like his old self, though. He had a 3.17 ERA overall in 28 starts with the Detroit Tigers and the Los Angeles Dodgers.

Now, Flahety is 30 years old and is coming off a season in which he had a 4.48 ERA in 20 appearances for the Tigers in 2026. The righty is going to be a free agent this winter and certainly shouldn't cost a ton after having a tough 2026 campaign. If he decides to settle for a short-term deal, the Cardinals should oblige.

He has the talent to really help this young rotation out. Then, if St. Louis sold at the deadline again in 2027, he'd arguably be an even better trade chip than May was, if he could stay healthy. Flaherty has had success in St. Louis. Now, he's a 10-year big league veteran, and yet he's still just 30 years old. The Cardinals could use an arm and Flaherty needs to rebuild his value. It would make a lot of sense for the two sides to come together this winter.